


A Night with Mr. Greg

by AbelQuartz



Category: Steven Universe (Cartoon)
Genre: Anal, Anal Play, Anal Sex, Ass Play, Beards (Facial Hair), Bears, Belly Kink, Biting, Body Hair, Breathplay, Choose Your Own Adventure, Communication, Crying, Daddy Kink, Deepthroating, Dildos, Explicit Sexual Content, French Kissing, Gay, Gay Sex, Hair-pulling, Hook-Up, Hotel Sex, Kissing, Large Cock, M/M, Moaning, Nipple Licking, Nipple Play, Oral Sex, POV Second Person, Painful Sex, Rough Body Play, Rough Sex, Spanking, Spit Kink, Tongues, Top Greg, Twitter, Underwear, Vibrators, Work In Progress
Language: English
Status: In-Progress
Published: 2020-12-16
Updated: 2021-03-10
Packaged: 2021-03-12 16:08:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 21
Words: 18,332
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28763097
Author URL: https://archiveofourown.org/users/AbelQuartz/pseuds/AbelQuartz
Summary: Want to join the fun? Head over to "a-night-with-mr-greg.tumblr.com" to keep up with votes and uploads!YOU — yes, you! — are a younger gay man on the outskirts of Empire City, responding to a message by a nice older dude on your app of choice. From there, though...what kind of man might you be? Who is this Mr. Greg? Grow and learn and waste the night away! Your choices as an audience drive the story!Updates every few days until completion. Enjoy while you can!
Relationships: Greg Universe/Reader
Comments: 2
Kudos: 33





	1. Checking In (again?)

**Author's Note:**

> READ THIS IF YOU'D LIKE TO JOIN:
> 
> Would you like to be part of the process? Head on over to "a-night-with-mr-greg.tumblr.com" and follow the votes as they happen! Each part will have a subtitle and a link to the current vote over on Twitter. Comments are welcome, but won't sway the vote—only your votes will do that. We're going to continue until we reach a definitive stopping point. If you have suggestions, ideas, or things you'd like to see, asks, DMs and comments are all open. Those aren't guaranteed to sway the vote, though. I want to open up paths based on what people have shown themselves conducive to liking, as well as a variety of sexual tastes. Specific kinks probably won't be included in this one, but in the future, who knows?
> 
> If you're reading this from chapter/part 8 onwards, keep in mind that I was going to upload this when it was finished originally. Instead, I've decided to open up my audience to AO3. So, sorry about involving you all so late in the process, but better late then never. Progress is progress!
> 
> Thank you all for reading! Enjoy the Greg goodness.

Parking might have been a nightmare, but at least you’re set. Relatively. The car’s locked and the garage is as secure as any garage can be in the city. At least this time it’s on the outskirts and not in the heart; Empire City is full of jacked-up prices for guys that aren’t worth their salt. 

The elevator begins to rise up. It’s nicely furnished, and this whole hotel is on the upscale side. One has to wonder what kind of guys are willing to rent out a whole hotel room just to have sex for one night. Or, there’s a chance that he’s staying for more nights, and that he’s got a string of men lined up one right after another. The thing is, though, he doesn’t seem like that kind of guy.

You pull out your phone and bring up the profile again, the one that’s now less than fifty feet away. He’s definitely your type, at least, a big man with a nice beard and no strings attached. The beach chair and the guitar are a little goofy, but in an endearing way. At least the jorts are ripped. He reminds you of a little league coach, or a rockstar, someone who used to be cool and has accepted that they’re not gonna hit that stride again. Actually, he is a band manager according to the profile, so that second one might not be that far off. His eyes are dark and his hair is shorter, at least the hair he’s got left. It’s all the more evident in the shirtless picture he sent you once you exchanged numbers and agreed to meet. There used to be muscle, but now it’s all belly, and his smirk says that he’s eager to get back into the scene. Maybe you shouldn’t have talked about DILFs so much. Damn you and your big mouth. Hopefully, it’ll come in handy, although you haven’t seen anything yet. He didn’t ask, and neither did you.

The elevator bell rings. Stepping out into the hallway, you turn to the right, heading down the hall. Nobody prowling these halls would stop to give you a second look, but even if they did, it doesn’t matter. It’s been a long time since you’ve seen a guy like this, and if you want to shoot your shot, now’s the time. The carpets give beneath your shoes. Something’s twitching down there, already excited to get a piece of that. 

Once you reach the door, 721, your heart starts to bump a little. He said he would meet you here, and indeed, you can hear music playing behind the door, nice and soft. It’s muffled, though, and you can barely make it out. These walls are pretty darn soundproof. There’s a chance that he picked the hotel for that reason, right? Is he a loud lover? Does he like dirty talk a lot? Or, is he worried about getting caught here. That doesn’t seem to be in his character, not like the well-spoken man with some minor technological trouble. He was nice enough to work around your schedule, and to get you a freakin’ hotel room on top of that. Some men are nice in talk but messy in person, though. Ugh, no more Jersey tourists in your apartment for sure. 

There’s no need to be nervous, or at least that’s what you tell yourself. People have sex and hook up all the time. Your roommate knows that you’re out and that you’ll probably be back before the end of the night. Nothing bad’s going to happen. Your hand raises, then hesitates…

Getting his attention is easy, you just have to

**> > Text him and let him know you’re at the door.**  
**> > Walk right on in! He’s probably ready.**  
**> > Knock politely, like a good boy.**


	2. Meet & Greet

**> > KNOCK**

He’ll appreciate that, right? After all, you’re a guest of sorts. Your knuckles make a quick rhythm on the door, and then you step back. You can’t help but put your hands in your pockets. That moment before a hookup is always a little strange unless they’re a repeat offender. And sometimes, those are the worst guys, the ones who want to hang around after like you’re just above friends but just below partners, homosexual limbo. What’ll this guy be? You don’t have any more time to think as you hear the footsteps and the door handle turning.

Of course he’s smiling as he opens the door. He stands aside, straightening up. Huh, he’s a little taller than you expected. He got dressed up for this, it seems, or at least he’s changed out of the jorts. A fresh pair of slacks don’t do much to hide the fact that he’s wearing white socks with it. Still, the shirt is nice, a short-sleeved button-down, a nice shade of presentable minty green. There’s still a little stiffness in the back of his hair from where he showered, probably just dry now. What are you, some kind of gay detective? He’s dressed up for you, and that’s all that matters.

“H-hey!” he says, straightening his back. “C’mon in, I bet it’s chilly out there.”

You thank him, and come into the hotel room. There’s not exactly a theme with something as commercial as this place, but it’s got abstract paintings, a nice big bed with the comforter taken off and folded, a giant TV, and…hm.

“Sorry, I hope you like a little, um, a little atmosphere,” he says, closing the door behind him with a click. “I forgot that most hotels have music channels. But I like the analog sound. Nobody really plays _The Philosophy Majors_ anyway.”

Indie music is alright. The guitar’s got a soft noise, and it’s almost romantic in a way. The smirk in his pictures was enough to show that he’s got a nasty streak in his own way, unless that was a front. From the look of things, though, he’s just trying to be accommodating. On the writing desk, there’s an partially open travel bag, a jacket on the back of the chair pushed into it, and in the corner chair there’s a small backpack with a sleeve hanging out of it. Looks like he’s spending the night regardless of whether or not you stay through it all. There’s plenty to do in the city, you guess.

“Also, um, I’m Greg. Greg Universe. It’s good to meet you.”

You turn, and he’s got a hand extended. He’s making eye contact, too. Wow, he really is personable. This whole setup with the room and the music and the cleared bed for play? It wouldn’t be surprising if he offered room service after. With Greg’s hand out and ready for you, there’s really only one thing to do, right?

**> > Give him a hearty handshake and tell him your name!**  
**> > Go for a big hug! He’s friendly enough to appreciate it.**  
**> > Pull him in for a kiss! Show him what you want.**


	3. Contact

**> > HUG**

With a little push forwards, you’re in his arms. Or rather, he’s in yours. There’s a lot of man to go around here, but somehow you manage. And he’s exactly what you hoped he’d be. Your chin barely reaches above his shoulder, and your hands are straining to get around his torso all the way. Greg makes that surprised dad sound, somewhere between a grunt and a gasp, and you’re sure you’ve heard it before but you’re not sure from where. It’s not until his arms awkwardly come around you too that you realize how much belly there really is. It’s just like how you imagined it would be from the one naughty photo. The shirt is nice and soft, barely containing the skin and muscle underneath. When you breathe in, you can smell the fresh fabric, and the remnant of the hotel soap.

Greg laughs a little after the moment’s passed, but he doesn’t let go. The awkward chuckle is as much of a transition from the handshake as he can make it, some semblance of connectivity. Right before the twinge of queer embarrassment comes to your cheeks, though, the arms squeeze just a little harder. His chest rises underneath you, and he lets out a deep but quiet sigh. 

“I know the feeling, kid,” he murmurs. “Been a long time since I’ve been with someone like this. I haven’t even… Yeah. Been a long time.”

You know the feeling, you say. Oh, right, the hug. And, of course, you tell him your name, just so you’re on the same ground. Before you can apologize for coming on too strong, the arms tighten again. 

“Well, it’s very nice to meet you. H-heh, sorry if I get a little nervous. I’m usually not up for this sort of thing! But now’s the right time, I guess.”

The right time?

“My kid’s moved out, got a new job, just need some peace in my life,” Greg murmurs. “And I guess a little romance. Or lovemaking. Listen to me, I sound like I’m a prude. We didn’t really have the apps and stuff when I was your age.”

You’re not exactly eighteen anymore, which you’re quick to remind Greg of, and the man chuckles again, shaking his head. Both of you have seen the kind of young people on that website. They’re not quite great at navigating the ins and outs of social graces. To their credit, though, you’re not that far removed. Old enough for an apartment, but young enough to be called ‘kid’ by the man holding you. 

It’s nice just to hug for a bit. You resist the chill of comfort that threatens to make you shudder in his arms. You don’t even want to _think_ about the last guy you tried hooking up with. Talk about disappointment… But Greg’s different, definitely friendlier, definitely broader, definitely stroking your back, definitely moving his left hand to your shoulder as his right plays with the hem of your shirt.

“Tell me if you need me to stop.”

Even though you’re not a musician, you know a tonal change when you hear one. His whole chest is resonant now, husky and full. The flirtatious man on the messenger was hinting at a man like this behind the words, but in practice, your breath is caught in your chest. Greg’s holding you like he’s been doin this every day, like he knows your body already. It’s crazy, but you’re starting to get the feeling that despite his dry spell he’s more experienced than he’s letting on. He breathes in against the side of your head as his hand slides under to the small of your back, warm fingers, a burning palm against your spine. As Greg starts rubbing your back, there’s only one thing you can do…

**> > Wait and let him explore your body, be patient and see where he goes.**  
**> > Turn your head and initiate that first kiss.**  
**> > Get busy with your own hands and ask about his last time.**


	4. Layers

**> > WAIT**

After all, he’s the one that needs your patience. He’s the one who hasn’t been with anyone in a while. It’s surprising, really, considering that he’s on the apps. You’d think boys like you would find men like Greg irresistible. Something says that he’s pretty picky about who he lets in, or at least that he doesn’t have the patience for spambots and text-speak. Grammar is bullshit, but communication is very real. For example, right now he’s communicating that his lips are on your neck, and that his stubble is pricking against your skin. The little involuntary gasp is enough to make him make some soft noise under his breath, an acknowledgement of sensitivities. Hopefully he won’t exploit that too much. At first.

Both hands are a bit of a surprise. Greg inches away and slips both hands underneath your shirt, the palms circling your lower back for just a second before grabbing the cotton. His eyes aren’t as devious as you’d expect, and the smirk is softened to a smile. Seeing your blank expression and the pink in your cheeks, Greg chuckles under his breath, then nods.

“Up.”

It’s not even a command, not quite an order, but he’s said it before. It’s like a parent telling their kid to put their arms up before getting them ready for bed. He did mention a kid who moved out, so they’re probably all grown up. Some things never change, though; and, point, he did have “Daddy” in his group tags. You try a smile back, but both you and Greg know it’s a little embarrassed and embarrassing in like kind. Your arms go up, and he pulls the shirt up over your head, up the sleeves, leaving your torso bare.

Thankfully he tosses it aside instead of folding it or anything. His clothes might need a little more attention, but he doesn’t seem to be thinking about that. The man rests his hands just under your armpits, holding you tightly as he backs over to the bed. Hotel beds are always a little high, but there’s enough give that he can let go and sit down fairly easily. Greg looks you up and down, and he’s letting that sexy edge back into his smile. The fact that he’s leading you is a good sign already, but that’s not a guarantee of anything. 

“Mmf. I’m feeling a little overdressed,” Greg murmurs, bringing his hands up to the top button of his shirt.

If there wasn’t enough dad evidence, you’re just now realizing that Greg had all his buttons done up to the neck. Those distractions aren’t anything compared to his legs angled outwards, his thighs straining against the fabric of his pants, the lump in the middle that’s angled just enough to hide what’s happening down there, the tucked-in shirt barely holding back the roundness of his belly threatening to break through, the tight white undershirt revealed through the buttons, the way he’s sinking into the mattress with his heft.

Man, you know what you gotta do.

**> > Take off his shirt! Start at the top and undress him, like he did to you.**  
**> > Take off your pants! Show him the rest of what you’re working with.**  
**> > Get on your knees! This is getting to your head, bad.**


	5. Good Boy

**> > KNEES**

The fall feels instinctual. Give yourself some credit, though; you’re dropping gracefully, drifting, even, down to your hands and knees. It’s a natural submission, but without being too needy, too whiny, too much of a pornographic stereotype. This isn’t some corny movie to rope people into a fantasy: this _is_ the fantasy, a real flesh-and-blood man in front of you, with real surprise on his face, a real smile warming up on his cheeks.

“W-whoa there, hey!” Greg chuckles. “I know what we’re here for, but I… I’m sorry, I’m still a little nervous. Dunno how to do this right.”

There’s no one right way, you tell him, don’t worry. Just him being Greg is all that matters. Both of you know that’s why you’re here. It’s a little physical, a little emotional, a tiny bit cerebral. The wavelengths are right. He sighs, slowing down with the buttons. One hand leaves to cup your face, and you close your eyes, raised up from your dog-like position back to just a crouch. The man undoes the last button one-handed, as his other pulls your face to his belly.

“I’m glad you like older guys. It’s still a little weird knowing there’s a bunch of people out there who have a—a thing, I guess. Just lemme know if it’s too much, okay?”

Too much? Too much what, exactly? Greg takes a breath, and you can feel his torso fill with air, expanding his gut and pressing against your cheeks. The lines of his undershirt are making grooves against you, impermanent marks. He sloughs off one sleeve, then switches hands to hold you as he shakes off the other. The shirt is tossed to the ground. You bring your hands up and rest your arms around his waist, as he holds you close with his left hand and strokes your neck with his right.

“Can I say you’re a good boy?” he whispers. “A good boy for…daddy?”

There it is, a touch of wavering softness. He’s already asked if you need to stop twice now, and you can sense something deeper inside with every inhalation. He wants something, something either rough or new, something he hasn’t done for a long time, maybe ever. If it’s been a while, he’s never had a partner he could call a ‘boy,’ not someone quite as young. Certainly he’s never had anyone call him ‘daddy’ except online. Of course, you say, nuzzling his belly. Greg shivers, just for a second, a little bit of lovely horniness rocking him solid.

It’s nice to be somebody’s first. Greg’s definitely been around before, but never with someone like you, and never after such a spell, if he’s to be believed. He seems honest, though, and really he’s just too sweet. However long that lasts remains to be seen, but. For now, he’s just content to let you snuggle and stroke. Whatever fire you can feel inside Greg, though, Greg can feel inside you. He leaves your neck for just a second, sliding the tank-top up to let you get against his skin. It’s warm, so beautifully warm, the cotton pulling out from your cheek to give way to pure dad belly. The soft curly hair, the unquestionable human smell, the echo burning against your ear that’s so full of fat and muscle… He knows, he definitely knows. You can hear his humored growl all the way down here, and your jeans aren’t gonna last much longer. 

Your hands are metaphorically twitching. You need more dad, more Greg, without any inhibitors. Where do you wanna go?

**> > Backside! Let’s see if he’s got as hairy an ass as he does a belly.**  
**> > Frontside! Daddy’s packing, and you wanna unwrap it.**  
**> > Upside! There’s some meaty chest you need to get your hands (mouth, too!) on.**


	6. More than You can Chew

**> > FRONTSIDE**

Your hands demand it. Actually, on second thought, why let your hands have all the fun? Greg sucks in a little air as you slide your face down the belly, letting your cheeks grind against his gut on the way down. Your arms come around naturally, supporting you back on the ground. But it’s time to let your knees do the work, shuffling a little against the carpet as your face slips into the space between his stomach and his waistband. 

As if on cue, Greg leans back and removes his hands from you entirely. You’re a self-motivated young man, after all, and he knows you’re up to the challenge. Well, it won’t be too much of a challenge, hopefully. Sometimes a guy makes you work for it, but you’ve handled your fair share of adventures before. When your face gets down between Greg’s legs, you can start to feel the outline, hardening up under his clothes. Hm. It’s hard to tell right now, but something’s peculiar. No, that’s not the right word. Worrying? Only one way to find out.

Getting the button on his slacks undone is easy enough once you manage to pull your face away. He’s just smiling down at you now, almost curious. When your fingers separate the button, your heart jumps a little as the front of his pants spring apart from the tension. There’s enough body there to make the zipper start to glide as Greg breathes out. You help it the rest of the way. His underwear isn’t anything special, box-brand navy cotton, one step above tighty-whities and not quite fashionable. But it’s a dad look, and it’s not so much about the bottoms as what’s underneath them. 

To your surprise, he stands to let you pull his pants down all the way, and you oblige with the rest of it, slipping off his shoes; socks you can deal with later. The problem’s staring you in the face now. Despite how much the briefs want to contain him, there’s already a small circle at the apex of his bulge, eagerness on tap. You’re so caught up with the image that he takes you by surprise as he grabs the back of your head and pulls you in again. Your fingers tighten around Greg’s thighs as he pulls you into his bulge and presses you there, grunting over your little gasps. The side of your face moves the hidden thickness, warmer than you thought possible. Still, you have to hold on. It hurts with each rotation of his hips, every single grind pumping your own erection. It’s bad form to get out of your clothes before you’re told, but damn if it’s not hard to resist jacking off to this alone; later, for sure.

Right now it’s time to be brave. When your hands come around, Greg lets his own slide gently to the back of your head. The grip on the tight waistband is as solid as you can make it right now, and you’re allowed to lean back just for a second as you pull the front of his underwear down all the way. Your heart sinks into your chest.

The cock that springs up isn’t too much longer than yours, but it’s solid all the way down, a consistent and terrifying thickness. If you were to open your mouth up all the way, you know you could start with the head, but even then, how far down can you actually go? The swollen testes are nestled neatly under the light brown of his pubic hair, and once you pull the briefs down you reach up and gently cup them, feeling their heft. Those, well, those are definitely bigger than yours. When he’s as hard as this, you know his foreskin’s all the way back, but the head betrays its health, almost red with turgidity, glistening in the hotel light. The only thing overshadowing Greg’s cock is his belly, and his face above that. Seeing your expression, his eyebrows raise for a second before his whole demeanor softens. He scratches the back of his neck nervously, laughing under his breath as he strokes your hair.

“Sorry, bud, I know it’s a little much at first,” Greg says. “At least I’ve been told. Honestly, I never thought it was…”

No, no, you say, it’s wonderful. If he’s blushing, the shadow and angles make it hard to tell. You shift your hands to his hips again. Well, this is what you came here to do. Your own cock strains with satisfaction as you open your mouth and let the head start to slip across your tongue. Immediately you can taste that familiar love, the flesh of another man, the warmth and salt and perfectly smooth texture. Immediately after, your eyes squeeze shut as you try to get the rest of it into your mouth. Greg doesn’t have any curves (well, penis-wise) to help ease it down. He’s the stiffest you’ve ever seen another person, and it makes the penetrative aspect more difficult than you thought. You have to consciously widen your mouth, curling your lips carefully as the head brushes against the roof of your mouth. Christ, you’re not even halfway down. 

The incoming groan is a signal, but the hand on the back of your head is an alarm. Your grip tightens as Greg begins to push you just a little more.

“That’s it, open your mouth for daddy…”

You’re trying, but the tears are pricking your eyes already. There’s actual effort on Greg’s part as you try to accept the pressure. All the cocks you’ve sucked before seem limp as plastic bags in your memory compared to what Greg is working with, and none of them have presented this kind of thickness. Holding on isn’t working practically. Right as the first choking sound starts burning your throat, you tap against the man’s hip. Fast.

His hand lets go immediately. Reflexes help you withdraw with care, sticky noises filling your eardrums as the shaft pulls out back across your tongue. Once you’re free, you pull yourself closer to Greg and hold on tightly, catching your breath, coughing out your sore throat. Well, that’s not going to work practically, not without some pretty intense training, or damage. And you were hoping to make a good first impression, too. A little laugh escapes you, and Greg holds on, stroking himself with one hand and holding you with the other.

“Whoof, sorry, I got in the moment there. You’re not hurt, are you?” You shake your head. “Okay, good. That…that’s good. Oh man.”

If anyone he’s been with has ever taken that without trouble, you want to call them up and ask them how the hell they did it. But again, years ago. Here and now, the man’s all yours. He pulls you back to the bed and sits down again, bare hairy ass on the sheets. This time, he lets you go once more, and he’s taking his socks off now. Greg seems a little lost in thought, as if he too is wondering what to do now that decimating your throat is off the table; being human isn’t easy. Watching him lift his legs, you know he’ll be completely nude in a moment. You’re the odd one out, but maybe that’s how he wants you. He hasn’t said anything for or against it, right? Daddy would tell you, unless he’s just waiting for you to take the initiative. Shoot, these are some mixed signals that you’re making up in your own head to combat your nerves. Once again, being human isn’t easy. But the hardest part’s just started, and you’re confident in your ability to…

**> > Finally strip so you’re both naked! When in Rome…**  
**> > Try sucking him again, but with a less damaging technique.**  
**> > Actually ask him what he wants, since you’re a good boy.**


	7. Junction

**> > ASK**

The socks have been tossed, and as they thwump against the floor, the question leaves your mouth. So, what do you actually want? He pauses and stares for a second, brow furrowed, as if he’s done something wrong. You clarify quickly that you want to be a good boy, you want to do what feels right, that messing around is fun but you know, this is mutual and all that. Greg’s face tightens for just a second before he smiles again, softening up everywhere but down there. He slides back on the bed, leaning into the mattress as he pats the space next to him. 

“C’mon up, kid.”

Well that’s as much an order as any. You get yourself up onto the bed, standing over shaky knees. As you get up, Greg lays down himself, the ends of his legs dangling over the end of the bed. The heft of his cock makes it stick out and bend back towards his belly, but at a distinct angle, barely bumping the fat as it spreads out. He catches you staring, then catches you as you lie down next to him, one big hand on your back.

“First things first,” Greg mutters. You smile awkwardly as he moves a hand to your pants, unbuttoning them deftly. Well, it’s just a little force, but it’s nice that he knows what he’s doing. He unzips you and starts to pull them down to fall off to the hotel floor. He smirks, and you know that he’s seen your [briefs](https://twitter.com/abel_after/status/1345870820170727426) before, or at least the type: not quite sporty, distinctly gay, more colorful than anything in a box-store package. At least, when he moves his hand back up to your stomach, you can take it upon yourself to bend your legs and de-sock yourself.

You say that you know it’s a little weird to ask now, considering that you’ve already been through a bit, but Greg snorts and shakes his head. “Nah, I’m just glad you asked at all,” he sighs. “Truth is, I don’t really know what I’m looking for. Just throwing spaghetti on the wall to see what fits.”

He glances up and meets your eyes. Yeah, maybe that wasn’t exactly the cleanest mixed metaphor, but it makes sense. He grunts and leans over, turning on the bed until his belly’s touching yours, warm against you. One hand props up Greg’s head, and his other strokes your torso, just tracing you, thinking out loud. It’s hard to imagine a conversation going places when his dick is nudging you as well, resting on your thigh like it’s asking you a question.

“Like I said, all the sex stuff is weird these days. You can explain all the nuts and bolts, but like, if my kid asked about daddy stuff? I don’t know what I’d tell him! I couldn’t explain it at all!” Greg says. “Don’t think anyone would like me trying it out, honestly. But it makes me feel good, just…thinking about it. Being big and strong and making people feel taken care of.”

He pauses, and you can see him lost in thought for a moment. You’ve grown up relatively internet-savvy, and it’s no question that Greg isn’t anywhere close to that. With the number of public fetishes and the amount of stuff available online, it must be overwhelming. Gay history’s taught you enough about the past and how things used to be, how the underground was. Now that it’s all here, well, what can a man do? At least you’re young enough to grow up with that before it overtakes you, but Greg, well, the gears are turning. When he looks up, he catches your expression, and his cheeks redden as he pats your side. 

“Oh, you don’t wanna hear an old man complain about stuff,” he mumbles, trying to smile. No, really, it’s okay! “Yeah, yeah. Look, I…I hate to ask, but there’s a lot of things I kinda tried out a few years ago. Might be rusty.”

Things? Well, that’s ambiguous. Where does one start with that? Regardless, it’s what he wants, a little experimentation. It’s all part of being a good boy. You affirm, and Greg smiles, then twists his body a little. Now this part you’ve done before.

You close your eyes as Greg’s lips meet yours. He starts slow, almost in thanks, firm against you. There’s plain lip balm with a touch of honey, appropriately bearish, just a little hint about how much he’s cared for you tonight. One hand supports your head to bring it up, and one presses into the mattress. Your own hands are occupied, the right resting above you, spread and sinking down, the left trapped underneath where Greg is leaning. 

He parts your lips with an unspoken question, and you let the kiss deepen, tongues meeting each other. You can’t quite remember your first kiss like this, but it wasn’t as full, certainly not as kind. Greg’s as experienced as kisser as he is a lover, and the warmth in your mouth is as strong as the rest of him. Every part of the man’s body seems to match: the thick beard, the broad shoulders, the round belly, the intimidating cock, and his tongue is just as wide as the rest of him, sliding along your own. The hand that had been pressing into the mattress drifts down, and he’s squeezing you now, resting all his hand on your body. There’s enough coverage to make you feel that he’s bigger, always. Nothing wrong with that.

And there’s nothing wrong when he reaches down under your waistband, either. Your hands are aching again. As his fingers press against the top of your groin and start to move down, you move with purpose, to…

**> > Mirror the motion and start to stroke him as well!**  
**> > Push forward, and get yourself on top on him!**  
**> > Pull him over and feel that dad weight!**


	8. Held Tight

**> > PULL**

You have no idea how much Greg weighs, but it doesn’t matter. The element of surprise and a good tug is all it takes to get him from ‘laying down’ to ‘laying on.’ A small grunt of surprise slips from his mouth into yours as he finally rests on your body. The hand that was about to stroke you has to come up and support his weight, but no matter, because just about everything is covered in a sudden flood of dad.

It’s unbelievable how warm his belly is. Every part of him is so big up close. The arms rising up underneath your pits to hold you in a hug are firm and hairy and strangely tan, a farmer’s tan—very dad-like indeed. You can hear the bed creak underneath you as his legs bend, knees supporting him just enough to not literally crush you into the mattress. His gut is firm in concept, but he’s letting it go, crushing your abdomen with all the glory his body can offer. Greg spreads over you like butter, smooth and lovely, grinding himself on the lower part of your torso. You don’t want him to pull away, not as long as you’re kissing, but when you need to you can imagine the wetness left over.

The present wetness is between your mouth. Greg kisses like a pork roast, or a crisp apple, just enough tenderness to make the juices flow. He’s not drooling over you, not exactly, although you have to admit you’re not opposed to a little sloppiness when things go further. No, it’s merely moist, tongue on tongue. His body is like yours, full of hunger; you can feel him return to this place of familiarity that he hasn’t seen in some time. The man’s body pushes and pulls and his lips roll with them against yours.

It’s safe to say that you’re just as hard as you’ve ever been, and you have to let go for just a second, sliding your hands down Greg’s sides towards your underwear. He was going for it before, but you interrupted, and now it’s your turn to show what you got. Greg rises just enough for you to wiggle and let your legs twist near the end of the bed, enough to let you slide the briefs down your thighs and off your body, kicked off towards who knows where.

There’s that feeling again. With your hard-on swinging up and pressed between your bodies once more, Greg comes back and doubles down on how close he wants to get with your mouths. All of his body is in motion now, holding you as you grip his shoulderblades right back, pulling away just to groan before you feel your lips sink back together, and he’s rubbing his hips on you. Grinding, frotting, whatever you want to call it, everything that he’s doing is calling attention to the fact that [he’s got something you don’t](https://twitter.com/abel_after/status/1349157825117880322). You wouldn’t call yourself ‘small,’ but compared to Greg, everything is small for sure. The girth dwarfs you, width squashing width, and he’s definitely got extra length in the glans at the very least. And either his balls are swollen from years of abstinence, or he’s just got hangers.

The senses are almost overwhelming you. The taste of someone else’s spit, the scent of a confident and fulfilled daddy, the weight of his body making you imprinted on the mattress—for a moment, you have to let go, stretching your arms above your head as you let your body spread out as much as it can. Whatever ends up happening, look, this much is satisfying by itself. Being naked and kissed and called a ‘good boy’ by one of the few genuinely nice men on the internet is pretty awesome in your book.

On top, Greg’s hips circle back, as if trying to get your cocks more together. It’s a teasing motion, where he’s rising and pressing down, ensuring that your body is absorbing the brunt of his frottage while your penis is utterly covered. And then his hands move. Your head is tilted back just a bit into the sheets as Greg pushes his body forwards, taking the kiss with him, and his arms are moving up as well. In moments, you can feel his hands grabbing your wrists, pulling them apart from one another above your head, with just a little weight added on. When he presses, you take in a sudden breath, small enough to show that you know something happened, but not enough to be a gasp. It’s involuntary, but Greg slows down anyway. 

As he pulls his face apart, you can see the blurriness he’s blinking away, the smile, the little bits of sweat on his forehead and the aerated bubbles of drool in his beard. “I… You doin’ okay?” he whispers. You assure him, but he can tell. The man looks up to where he’s holding you. Before you can reply to the gaze, he slips away, pressing himself down into the mattress for just a little more distance. 

“I know we, um, I know I’m trying the whole ‘daddy’ thing, but I-I’m still kinda new,” Greg says quietly. “I don’t want to do something wrong, especially when you’ve been such a good boy.” 

Well, that sends a wiggle through you, and both of you pause to chuckle quietly. Still, Greg swallows and blows a cool, nervous breath away from you.

“How…rough do you want me to be? I’m still gonna stop when you say stop, by the way. No safewords or any of that. No means no. Okay? But if you want me to be that kind of daddy, I will.”

Even with your wrists released from his grip, you can feel his nervous energy. Honestly, you think, even if Greg wants to start out there’s a chance he’ll have to stop himself. Or, if he goes further, his inexperience might not be to your benefit. Then again, you’ve both established you’re in a mood, and he’s going to listen; tonight’s all about you! You take a big breath, the air swimming with dad, and tell him…

**> You can be as rough as you want tonight, daddy.**  
**> I think the best thing to do is go slow and gentle.**  
**> Maybe I can show you what I know about rough stuff.**


	9. Tensile

**> > ROUGH**

He raises his eyebrows, and then...blushes a little. Maybe you expected a wicked grin, or some kind of sultry laugh, but probably not that. Greg bites his lip and looks down at the bed, rubbing the side of your wrists with his thumbs.

“I do love that, don’t get me wrong, but, um,” he says softly, “it’s been a while since I’ve been rough with anyone, or anyone’s been rough with me. Things have changed, I guess. You’re...not the kind of guy who wants me to actually beat you up, right?”

No, definitely not, you know better. “Yeah, I figured, but I don’t know. I… Just me patient with me, that’s all I ask.” How could you not? It’s always fun to see a daddy warm up a bit. You reassure him, and he smiles, adjusting your bodies so that you’re lined up with a little less weight off of you. Not that you were complaining about that, but it makes you less malleable. Greg gets his knees into the bed and takes a deep breath, on all fours over you. “Lemme see.”

The first order of roughness is with his hands again, his right hand, reaching up to stroke the side of your face. Alright, you can’t help but laugh just a little bit, and he chuckles in return. It’s the small things that make the exploration what it is, a little fun romp through the things you know you love and the man here to make them all come to life. The back of his fingernails drifts over your face, tingling warmly around your ear and jaw. Greg takes one deep breath, then slides his hands up towards your forehead. 

And he doesn’t stop. The fingers drift through your hair, almost petting you. But you already know what’s coming, and you can feel Greg’s fingers curling tighter, and tighter, until they’re pulling at the hairs just past the tips. Pressure is concentrated in a thousand places on your scalp as he pulls you back and almost upright, lifting you off the bed and forcing you to choose whether or not you’re going to support your body or let your head burn. You open your mouth in a prolonged grunt. When the man brings his mouth down, it seems like he’s using you for a kiss.

But no, this is a kiss on your neck, just on the side, a piece of tenderness to ease you from the pressure of his grip. As his left arm snakes around you, though, the kisses open up, and you’re held tighter, until his lips pull back and you feel the mounted pressure of his bite right on the muscle. You hold him with both arms in a split-second, making sure he doesn’t let up, before you let out your little yelp. 

Greg knows how to hold you, and this is how he’s easing into the pressure of being a daddy, it seems. You can’t move with him holding you down, and you can’t tear away from his body on top. Your eyes begin to water just a little, from the burning, snarling hold on your neck combined with the tug of your hair. In this position, Greg has to rotate his arm, releasing your scalp just for a second before pulling you away and exposing your neck to him for a deeper bite.

This is the kind of roughness you’re looking forward to. Your body rises from the bed, pressing with need into the man’s stomach, rubbing the bottom of your cock against the coarse hairs. Greg’s legs pump back, all the muscles around his hips rocking to keep you down. His cock shoves and pushes your body away, but the warmth magnetizes you closer, making you draw towards its thickness. You can almost feel his heart pounding in his torso, a broad and hairy chest built by time and isolation. Every part of him is made for you. He draws back just for a second with a wet release.

“You wanna be a good boy?” Greg grunts. “Well I wanna be a good daddy. What’s daddy got that you like? What does my dirty boy want?”

There’s just a slight intonation shift, a bit of play, a little nastiness that makes your fingers dig into the muscles of his back. Obviously Greg’s got a lot to love, but if you make a list, you already know he’s going to make you choose. He bites down once more, and forces an answer out of you:

**> > I want to play with your cock!**   
**> > I want to feel the weight of your belly!**   
**> > I want to get my mouth on your chest!**   
**> > I want to grab your ass!**


	10. Roundabout

**> > BELLY**

The bite increases, then lets up slowly, and Greg makes a noise like he’s thinking. You’re still panting a little—oh geez, hopefully that’s hot and not weird—and the shared sounds of the lovemaking are filling the room and your ears. You can tell that the man’s thinking, although you’re not sure what’s on his mind, exactly. Finally, his mouth lets go.

“Alright.” He takes a deep breath. “Okay. You sure? I-I mean, you sure that’s hot?”

Why wouldn’t it be? But you don’t ask that aloud, that feels condescending in response to a genuine question. Strange, considering that when you hugged him, you were right up in there. But as Greg pushes upright, you can see his expression, and it’s almost funny. He’s smiling as if this is the first time someone’s ever complimented his gut before, as if he can’t believe that someone would actually like it, and in this place, he’s willing to give it a shot. All the better for you, because looking down, there’s a perfect, hairy curve shadowing your body. You can’t help but shudder just a little.

Greg pulls himself forwards until he’s straddling your groin, and he sits up with a grunt, on his knees above you. His cockhead juts out above your abdomen, and his belly is above it all. He chuckles, a single curious laugh, and you glance up to see that his expression’s hardened just a little upon seeing you stare. There’s the rough daddy back again, with a little starstruck encouragement.

Then, his hands lift, until they’re digging into the bottom of his shelf. He pulls up into the fat, massaging himself, before letting his belly rest back down gently. His right hand makes a slow circle around as he watches you, forcing the entrancement, as if you need a spiral to be taken in by him. Greg starts to stroke himself slowly, tugging slowly with a thick, gentle fist, bringing the skin right up past the head before pulling it away again. He doesn’t need to, not with how hard he is already, but you can’t hide the little whine that bubbles up out of your mouth. The circling hand pulls away before he slaps down, smacking the skin and making you jump a little from the sound.

“You can rub it if you want. Go on, do it for daddy. You like big daddies, huh?”

 _Yes, daddy._ He moves his hands to his hips, letting his cock twitch freely. You’re almost shaking as you bring your fingers to the belly and let them sink in. Greg sighs as you start to rub, muscles and fat hot under your grasp. Your fingertips dig into the line underneath his pectoral muscles, tracing down the dome of Greg’s gut, before you go back to rubbing the sides again. The sheer heft is enough to make you feel faint, the way that you can push into him from a low angle and feel gravity and the flesh push back against you. It’s pushing harder now. Wait, it’s moving. You barely have the time to register a gasp before Greg’s hands come down as he falls forward. 

It’s a measured descent, with the dip of his bellybutton just under your chin as the rest of your face is entirely engulfed in stomach. All the groans you can make are stifled by fat, darkness and hair and the tingle of sweaty skin covering all your senses. Your hands slide up to hold the sides of his belly, pulling him closer to get the taste you were dreaming of. It’s too much, literally too much, cutting off your breath, but just for a second, your world becomes nothing but tummy, and Greg’s deep groan fills your face. Like a desperate dog, your tongue extends and licks the sweat from his skin, thick hair and masculine musk like a storm on your tongue. The texture is weird, very weird, but it tastes like Greg, like androphilia, like a daddy. You can’t hold your breath for too much longer, and Greg knows this, but he rubs himself on you just for a moment, small circles and pretend-penetration, with the length of his shaft throbbing on your collarbone.

You take the biggest gulp of air as the man rolls off of you, leaving your hands to fall down and grip your chest just to ground yourself. He falls to the side, and you blink back to the muted hotel lighting as he moves up the bed. You turn over and face him, on your own stomach, as he lies down, propping up a couple pillows at the head of the bed. Greg sighs contentedly, rubbing the hair on his belly matted by your spit.

“That’s a new one for me,” he murmurs, bending his knees up and out to stretch his hips. “Always thought that people wanted a ‘thick dad’ for the dick, or the butt or chest.”

Well, he does have those too, but your only verbalization you have right now is a little growl of appreciation, almost a purr. Of course Greg smiles; he knows what he’s doing to you. His cock hangs heavy from his crotch, glistening as it wobbles from the dense mess of hair at the base. It’s almost hairier around there, past his happy trail, past his balls, in between the hint of his ass underneath. You pull yourself up on your hands and knees, getting closer, watching him pat his tummy and close his eyes to catch his breath… What’s your next move?

**> Get up on top of his belly, be playful!**   
**> Get down and suck him, at your own pace.**   
**> “...can you turn over, daddy?”**


	11. Taste Test

**> > GET UP**

The best part about a hotel like this, besides practically everything, is the fact that the beds actually come with headboards. You crawl on up, getting yourself over until you’re almost hugging him again, until you can rub your face up and down Greg’s stomach, pressing your hands into the mattress. The man chuckles, running his fingers back through your hair, a little gentler this time. There are moments to get rowdy, and moments to just enjoy it.

Still, a little closeness goes a long way. And hey, nothing wrong with being a little cheeky. Greg raises his eyebrows as you don’t stop moving, your cockbrushing over his stomach as your pull yourself up and up, until you have to swing your legs over. Straddling a belly like this is pretty much par for the course with how this is going, just like how you’d expect the dream to go. If you put your full weight on Greg, it might hurt him, but once you get your knees down you can rest fairly easily. He’s warm underneath you, very warm. Your thighs shudder just slightly, just involuntarily.

“Heh. Good boy.” You know he’s just saying that, because you haven’t actually done anything that would warrant that, but it makes you grin a little anyway. Greg studies your body with a smile, bringing his hands up to your legs. You grip the headboard gently as his fingers dig in, squeezing your body and running his hands up and down your thigh, before his thumbs find your hips. The tips press right in on either side, the transition of torso to groin, right in that ‘V.’ It must have been a while since he last got a chance to explore someone’s body like this, and you can practically smell the appreciation wafting off of him.

Greg’s not laying all the way down, and he shifts back just a little more, as if straightening himself out. But at the same time, his hands move around to the other side of your pelvis, and you suck in a swift breath through your teeth as he starts to knead your butt. You’re a good boy and this isn’t your first time proving it, but it’s never expected, is it. All hands are different, and you can tell these apart from all the others. Greg has a musician’s calluses and time’s softness, practice in each finger keeping you balanced. Both hands bring you forwards, off the belly, and into the man’s mouth.

Really, the draw is almost sudden, even with the fluid motions. You barely have time to stutter out a quick _Oh, daddy…_ before Greg’s tongue is wetting the underside of your shaft. He might have said he’s out of practice, but he’s practiced before, and he knows how to work you regardless. You’d like to think it’s not easy to get everything in; then again, compared to the man underneath you? And for the moment, he’s pulled you in, lips open, his mouth warm and wet around you as he grunts and pulls you forwards until his beard brushes your balls. The gentle prickles of his facial hair poke you softly before he retracts. Just like the kisses, he’s wet with this, too, throat thrumming around you. You let out a gentle groan of your own as he pulls up, pulls back, pulls out and kisses your head before he tastes you again. Maybe if this were a quickie you could let this go for a few minutes before shooting, but Greg’s taking his time and you want this to last as long as you can make it.

Looking down, you can see him just enjoying himself all the way. It almost looks like he’s savoring a deep, expensive wine or a perfectly performed sonata. His eyes are closed and his brow is raised, furrowing in pleasure every time he hilts his lips on you. The picture is almost beautiful, in a way, a different kind of sexy. Just as you’re thinking that, he opens his mouth up, tightening his grip as he pulls you in just for a moment, growling and gurgling with determination as he shakes his head just a little, a dog with a bone, sucking all the goodness he can out of you. The warmth of his throat covers you entirely before he draws back, stifling a small cough. One point in your favor!

There’s no indication of how long he wants to go, but you can imagine that you’d be dripping a little and he’s getting a taste of how good he’s doing. The sensation of his lips pulling your skin back and forth over his tongue is so wonderful, even if you’re not getting the fully belly experience. Greg’s hands, though, are still stroking and squeezing your ass, pulling at your cheeks with as gentle pressure as he can muster all things considered. There’s energy in front of you, and energy behind you...

**> > Push forwards and really work his mouth! Greg can take it.**  
**> > Press back into his hands! Let him feel the butt. No, like, REALLY feel it.**  
**> > Pull up—to make your butt and his mouth finally meet...**


	12. Ready, Steady

**> > PRESS**

“Mmmf...” Greg’s moan emerges as your cock slides out of his mouth, a little louder without anything in the way. He can’t seem to help but chuckle as you lean back. It’s clear that you’re more into his touch than his pleasuring, even though you gotta say, you’re glowing from his expertise. There will be harder times to come, of course, but for the moment? He’s done good.

His hands, however, are picking up on the hints. Sitting back against his palms, you can feel him squeeze deep, around the fat and muscle, almost down to the bone. Even compared with Greg you’ve got a fair bit of meat back there, if you do say so yourself. The man grunts appreciatively and weighs you in his hands. It’s like a wave, this little ride, the way that you let your legs move up and down, the way he’s lifting and pulling, the way his fingers don’t quite go deep enough to pull you apart.

“Been a long time since I’ve felt this,” he murmurs, staring ahead, as if he can see through your body to where he’s kneading. “Literally, I mean. A nice ass. Didn’t know I’d be the one handling it, I honestly thought you’d be a little more… I dunno, bratty.” 

Interesting, considering you tried to be somewhat nice earlier. Was that the impression you gave to him over text? you ask. 

“No! No, it’s just...playing nice. People are different in the bedroom. We didn’t talk about who was gonna do what or even if we’d get this far. I guess...I should ask,” Greg said, clearing his throat. “Is it okay to go all the way? I-I’m, y’know, ready if you’re not.”

Sometimes, these sorts of things are left to the fates to decide. Sometimes, you know for a _fact_ that you’d never be caught dead going to a hookup where you might be bottoming without proper preparation. And you say as much: _I’m ready._ Before you can even worry if that tone comes across as both confirmation and desire, you feel Greg’s whole body shudder just a little underneath you. He already knows. Of course he does; no matter how much time has passed, the intuition never goes away.

Yours could use a little working. Not surprisingly, you’re caught by surprise as his gaze darkens, his smirk widens, and he sits up with a hefty grunt, steadying you just enough to keep you centered as he shoves you back onto the bed. The lights smear for just a second before you hit the mattress, a gasp forced out of your body. Clearing his belly and his legs wasn’t an easy feat, but somehow you managed, lying there with your freshly moistened penis standing to attention. Greg turns, sliding off the bed. You sit up just a little on your elbows, watching him eye his backpack in the corner.

He takes a deep breath, lifting up the shelf of his gut press down into his groin, pushing the fat back and making his shaft throb just a little—a reminder, or a warning? But Greg just looks over you once more. Gears are turning behind his eyes, and you can see them in motion as he massages his belly, bringing his hands up to squeeze his fat nipples, tugging them tightly before reaching down again, digging his fingers into the groove of his thighs. Sexual stimming, perhaps, preparation. 

“Turn over,” he growls. “You ain’t ready yet.”

You know that order well, and you turn your face away in deference, wondering if he’s going to ask you how you want it, how he’s going to give himself to you. But as you get on your hands and knees, as Greg stares down your body, the length of it facing him, he doesn’t say a word, just smiles and chuffs. One hand strokes himself, and the other goes back to the nipple, a thought process, silent machinations. You want to ask what he’s going to do, how he’s warming you up, how that thing is gonna get inside you.

Then again, sometimes, these sorts of things are left to the fates to decide.

**> > Time for a finger, nice and slow.**  
**> > Time for a tongue, nice and wet.**  
**> > Time for a spank, nice and hard.**


	13. Beat Red

**> > SPANK**

If there wasn’t something in the way, you might have been across his lap. As it stands, Greg’s standing tall himself, rubbing his belly as he comes up to the bed. The mattress is an examination table, upon which you’re steady and still, hands down, knees bent, the very model of doggy style. The man’s hands warm your body once more. Your spine is played like a piano, gentle fingers running up and down the arch. It’s like he’s smoothing you out, or perhaps calming himself. His cock is a good indicator of where his mind’s going even if he’s not actively saying anything. Greg’s breaths are deep and measured, a calm behind the slight tremble you can feel as his right hand runs down your backside. Or is that your skin shaking in anticipation?

You can’t anticipate the hair grab, though, a sudden twist of the fingers pulling your scalp up, and the gasp filling your mouth morphs into a sharp cry as Greg’s other hand pulls back suddenly. The impact as his palm comes down creates a deep sound, the melody of your body in submission, a staccato note played by reddened flesh. It’s not as pointed as a whip or paddle, but more meaty. Greg is meaty, his hands are meaty, thickness that squeezes your tender, tingling ass where he just hit. 

“If you want a rough daddy, you’re gonna get a rough daddy,” he says above you, as calm as he can make himself. “You want it?”

Your voice, your little _yes, daddy,_ is more muted than you intend, and before you can clear your throat, the hand comes down again, lifting up at the end of the impact to come back and prepare for another. You tell him again: _Yes, daddy!_ These are familiar tears, different in the moment but the tears of a good boy all the same. Of course it hurts, and Greg’s hands aren’t as gentle as they were when they hugged you, but it’s what you asked for, right? Fuck that, it’s what you’ve been craving. You hold your position, arms and legs quaking, your head held high still in Greg’s grasp, trying not to draw away. Even with only two spanks your cheeks are prickling with pain, raw and tender, probably starting to swell. Thank goodness nobody else will be seeing this for a while...unless you want to show off.

There’s no time to think about that, though. Greg’s musicality comes through, to the beat of the song in the background that you don’t recognize. The record player thrums along, and measure by measure, Greg brings his hand down, over and over. His hand isn’t long enough to cover both sides, so he alternates, a smack on the left followed by the right, front and back, full-bodied impacts that shake down your thighs. Each hit would have propelled you forwards if Greg wasn’t holding your hair still, just enough to keep your head held high. 

“That’s my good boy! C’mon! Lemme hear you sing!”

Past a certain point you can’t even tell that you’re crying, or that you’re yelling, a constant stream of quavering pleasure that would have said daddy’s name over and over again if you could form words.

But he misses a beat. Your voice stops for just a second, dying down before the final smack right across your ass, a full and forceful spank that digs deep into the muscle. One last shout of pleasure, and Greg lets you go. Both hands leave your body, and you collapse to the bed, dizzy and hiccoughing and groaning into the sheets. He really knows how to use his hands. Pockets of static fill your backside. The skin is loose but feels like it’s crawling with pain, and the muscles of your ass feel like they’re beat to jelly. There’s no doubt that Greg’s going to be smacking it more later, but not with his hands.

“God, fuck…” Greg shakes out his arms, or at least that’s what it sounds like. You can’t see much through the tears. Still, you can hear him stop. After something like that, the concerns are understandable. No means no, but it’s not easy to talk sometimes. You wrench your left hand out and give a thumbs-up. Both of you laugh softly, although yours is a little more waterlogged.

A daddy can’t help but be tender, though, and the man pauses, letting out air as he rubs your neck with one hand and your ass with the other, a gentler mirror. The discomfort of your erection pressed on the bed is enough to keep your in the loop, at least, but Greg’s also rubbing his cock against your side. It’s not over yet. His fingers are still curling, still pulling at your skin, still eager. He’s the kind of guy that won’t stop until he’s completely drained.

“My good boy,” Greg murmurs. “Daddy’s got something for you.”

**> > Another taste of cock, applied gently (with some encouragement)**   
**> > Some facesitting and dad-smothering (again, with some encouragement)**   
**> > Tongue, spit, and sloppy mouth play (with non-verbal encouragement)**


	14. Mouthing Off

**> > TONGUE**

Both hands take your body and roll you like a tire, pushing you onto your back. If it wasn’t for the slight twinge of soreness on your backside, there’d be no complaints to being manhandled. All the same, you can’t complain anyway as Greg swoops down, one hand holding your hip as the other curls under your head. The kiss is a pause button. His head seems to slow down for just a second before your lips touch. They press together, and you’re calmed, just a touch, just enough to feel how your heart is pounding in your chest.

He releases, he pulls away, and you both take a breath. Greg pauses to study you before he gently rotates your body on the sheets. You help to move yourself as much as you can because, well, actually getting dragged is just going to pull some muscles, even if he is strong enough to put you wherever he wants. Sitting on the edge of the bed, you can see Greg outlined against the lights by the bed, warmly lit, his belly eclipsing the opposite wall. The same belly comes forward and presses against your chest. What else can you do? You wrap both your arms around Greg and hug him tightly, listening to the gentle rumbles of his insides combined with the resonant growl from within.

One finger lifts your chin, then both hands come down to wipe your eyes. There’s a strange line between daddy behavior and paternal behavior, muddled just a touch as he chuckles over your own embarrassed giggling. But then, the hands grip your shoulders, pressing you back onto the bed. Leaning over the mattress, Greg’s body comes down with you, pinning you yet again, angling so that his mouth meets yours once more.

This is the kiss that gets your heart pumping. He barely asks, barely offers before his tongue worms its way into your mouth once more, forcing your lips apart as he pushes you with his lips. The sounds that are echoing in your ears are so loud, and so obscene, enough for someone on the other side to hear. You grab him around his back, and he holds your shoulders, and his cock and belly are crushing you to the point where you have to raise your legs; any lower and he could be fucking you. 

Greg sucks like he spanks, in motions that are measured and massive at the same time. Each wave of pressure from his lips pushes hot spit down your throat, and every time he pulls back it feels like he’s draining you dry. The bristles prick your skin, firm but not quite needles, not quite enough to hurt; Greg’s grown it out more than enough for that. Even after a few seconds of deep kissing it’s impossible to tell whose fluids belong to either one of you, flavored with lust and hot as hell.

Gently, Greg forces your mouth open a little bit, and a whine from your throat is stifled as he sucks on your tongue. It’s how you imagine he would treat a clitoris, or a sensitive cockhead for edging, a smaller nub that he wraps his lips around and slurps softly, pulling and teasing, as close as the organs can be. When he releases, the favor spurs you to action, and his tongue’s return to your mouth is an offer. Greg can read your mind, it seems, or perhaps he offers what he wants in return. Either way, you take your mouth and start to suck on his open tongue. Even that part of him is bigger than yours, wide and soft and covered in spit. Drool dribbles down the sides of your cheeks, and the muscle slips in and out of your lips, just a couple inches, barely penetration but as much as your mouths can make together. 

The man pushes himself up and out, a string of saliva connecting your faces. His lips curl as he takes his right hand, pulling at your lower jaw. Your oblige, opening up, and Greg grunts once before pursing his lips. The wet glob bubbles up before he pushes it out, and you watch it dangling for just a second before gravity pulls it, and the spit hits your outstretched tongue. It’s heavy in a way nothing else can be heavy. You pull back, letting the fingers rest just on the edge of your lips as you swallow. 

Can you be greedy? Sure, why not. You open your mouth just once more. Greg smirks, then puffs out his chest. Just when you feel he’s soaked up enough saliva, the man pulls his lips in, then spits, loudly, all over you. The concentrated fluids hit you like a shotgun, and only the fastest reflex stops it from going in your eyes. His warmth covers you, cooling to a thousand shivering slivers in less then a moment, soaking you in spit. You can only feel him lean down, and you whine as Greg’s tongue slides up your cheeks, one at a time, soaking up what he just spat there, cleaning you before getting dirty.

The lungs, your breaths, are almost in sync as he pushes up, staring down at you with a satisfied glower. You can see Greg’s chest heaving, and you know you’re panting yourself. His shaft is nudging your own, or at least what it can, considering that his belly is squashing you down enough, putting pressure on your cock and balls. He blows out a breath onto your face, then bites his lower lip.

“Are you ready?” he whispers.

You remember the messages between you, talking about lubrication and condoms, about testing and preparation, and you know he’s got a couple things in his bag. He’s pulled out all the stops, as much as you want for a first hookup, and he’s as hard as a rock. But if there’s one thing you know about Greg, it’s that he’s genuinely asking. Maybe you’re not ready, he’s thinking, maybe you want something more. He knows that you’re hard, too, but not everyone can quite hold up a hog like his. And yet, Greg’s also asking because he wants to fuck you. You stare at the belly, the twitching pecs, the spit-laden beard, the dark and excited eyes…

**> > Yes, daddy. I’m ready.  
>> There’s one more thing I wanna do...**


	15. Point of Entry

**> > READY**

“Mrgh.” He’s trying to smile, reply, laugh, and grit his teeth all at once, a silent _That’s what I like to hear._ There’s that wild underside, the part of Greg that had to be kept in control as he was spanking you. Maybe that’s worrying, or at least it should be. But like you said, you can handle a rough daddy. You reach down, stroking your fingertips along his belly, right before he pulls back and stands. Guess you’re doing it here, then. It’s a good position to start, to get it in and weigh the situation.

The man tromps over to his little travel bag, pauses, then adjusts the record player. The record skips for just a second before he sets it back to the first track. It’s a weird machine, part digital and part analog, vinyl for the modern era, new meeting old—just like you and Greg. As the funky bassline starts in again just a touch louder, the man visibly relaxes. You can see Greg straighten up and roll his shoulders, gently flexing his neck and backbone. The music’s in him, as it’s always been. Maybe he used to be a musician, hell, or even part of the band. When you catch a glimpse of his profile, you can see his face in a slightly better place, less worried about control and more about when to let it out.

“Legs up, boy,” he murmurs. You oblige, wincing just a touch as your reddened cheeks move with the command. At the edge of the bed, your butt is just underneath the perfect height for him to penetrate. Both your hands come up to support your legs, tugging the skin of your thighs and feeling your hold clench a little. You had some practice earlier, but without any extra preparation, the thought crosses your mind, the worry, that someone as big as Greg won’t be an easy fit. 

In fact, he seems even bigger now as he comes back, a pump-bottle filled with clear liquid in his right hand. Greg leans back and squeezes the top right onto his skin, before tossing the bottle onto the bed and working his cock. The muscles around your hole clench involuntarily at the sight of him grunting and oiling up the shaft, the hint of veins bulging out just underneath the surface, the redness of his head even redder now that it’s shiny and slick; it’s almost the size of a ripe plum. It’s hard to tell where the lube begins and the precum ends. You’ll be needing more than precum, though, and you take a deep breath. The sounds of lewd, oily manipulation fill the room in time with the music. Greg stands right in front of you and looks down at your hole, nostrils flaring as he masturbates slowly with a shaking wrist.

You want to ask if he likes it, but besides being a silly question, he lets go to grab the bottle again, squeezing it right down on your hole. It’s the first time he’s touched it while it’s spread, and you hiss in through your front teeth, offering a silent affirmation once your words come back. While Greg’s left hand is latched around his glans, working the lube into his mushroom head, his right tosses the bottle and rubs around you. It’s not quite in, never quite in, only teasing at the rim. Your whimpers fall on deaf ears. Greg stares with purpose.

Bare isn’t always how you roll, but a clean bill of health on your end was met during chats with one from Greg as well. It’s a considerate motion, taking into account the length since his last time here. Some things might never change, though, like the look in his eyes when he lets go of himself to grab your ankle before stepping up to the plate. If you didn’t know that he was concentrating and aroused, his expression would seem strangely angry. His brow digs into the bridge of his nose as he lowers just a little, grips his shaft, and edges the tip to your hole before the push.

And **everything** pushes. Even with the lube, your eyes squeeze shut tight, as tight as your hole against the force of Greg’s first attempt at penetration. Instead of giving in, the thickness makes your ring resist, squeezing around the very tip of the man’s cock without giving him any leeway. You open your mouth to ask if he needs you to move, but Greg pushes back on the hotel carpet with his bare feet, and in an instant, your suggestion changes to a sudden, pained cry.

The head breaks through, thick and slick and unforgiving, and starts to push into you. The length is no issue, but the girth, the sheer size of Greg’s shaft is almost too much to handle. Burning pain spreads around your hole, the muscles begging for another chance. Maybe with more control, maybe if he was—no, he’s already going slowly, groaning softly as he sinks inch by inch inside of you.

“Fuck, you’re t-tight,” Greg croaks, releasing himself to hold up your other ankle. “Tight boy for daddy, such a good boy…” 

Shakily, your hands reach between your knees to spread yourself just a touch more, but this is as spread as you’re going to get. It’s just barely too much for you and your ambitions. At the same time, as Greg’s belly encroaches upon your erection, no amount of anal reluctance can change the fact that you’re still rock-hard. You slide up, encircling your cock and balls with both hands and holding tight. Arousal can only do so much, though.

Your hole is so tight around the man’s shaft that you can practically feel his pulse. Greg has his eyes closed and his head in the clouds, and you know that he’s not going to stop until he’s hilted you, and then, then things are going to get rougher. Can you even take it until then? The sting of tension is impossible to ignore, and your eyes are already watering. The needle is wavering between ‘challenging’ and ‘too much.’ You’re aware of your bodies limits, and that fact alone is worrisome. Keeping that in mind, you know best…

**> > Tell him to go gentler. You need a soft daddy warmup.**  
**> > Ask Greg to pull out. Reevaluate how you’re gonna take this.**  
**> > Say nothing. When it gets to _really_ be too much, then you’ll tell him.**


	16. Ambition's Cost

**> > NOTHING**

‘Nothing’ is a bit strong. You can try for another little murmur of calling Greg daddy, or you could groan appreciatively, or you could say something dirty and flirty about your tight ass. If you could say anything at all, that is. You can’t unclench your teeth for the moment, and that’s not exactly sexy, but that’s what you’ve got going for you right now. All you can do is pull on your junk, getting it positioned before the belly comes down and smothers your taint instead of merely kissing it.

Greg’s concentrating, and enjoying himself, you’re pretty sure. The bliss of glancing down at your body combined with the open mouth says enough. The man leans back just a little, almost pulling out, before pushing back in. That should make it easier, but it really, really doesn’t. The girth is enough to pull at your skin no matter what he’s doing. Thinking back, you have to wonder if anything thicker has actually been inside of you. There was some glory hole business, and an old friend who was definitely long, but this particular combination is just about the biggest you’ve had, certainly in a while, and you’re no fist bottom. If this is causing you trouble, a fist is going to be hell. In the moment before he pushes in and deeper, you wonder if Greg would make a good fist bottom. Not many big daddies in that scene. Those synapses snap under the weight of pressure pushing you open once again. Is he thicker near the bottom? Are you even close?

“Fuck yeah…” the man murmurs. He’s got more dirty talk coming if you know how he operates, but his focus is locked. You have only a second to think about protesting once more before his hands come down to the line between your thighs and hips, and his grip tightens just enough. With a grunt, Greg brings you closer to the edge and forces himself all the way in. You’re sure now that it doesn’t matter how thick he is at the bottom, because all of it’s inside you, and it’s thick everywhere. The head is deep in your hole, and everything else is stretched to the limit and beyond. The relative suddenness forces your hole open, and the pain you had been worried about redoubles, swiftly and suddenly, a stabbing tension pulling at the edges of your entrance like a thousand hairs being plucked at once.

You can’t contain the yell, or the involuntary seizing up. Your hands grip the sheets underneath. No, you said you could work through this. You said that you could try it out. But it’s not going to be easy. This is close to the worst pain you could be feeling, certainly the most strenuous exercise you’ve put your butt through. The blood’s pumping in your ears, and you have to force yourself to breathe again. Even as the rhythm slows down, your hole is still burning, and above all that, the music is suddenly louder—no, things are quieter. You open your eyes, and through the blur, you can see Greg looking at you, and he’s not smiling anymore.

“You okay, buddy?” Opening your mouth, you offer something that sounds like affirmation, possibly, if it was words. You’re not okay , obviously, not physically, but you don’t want to outright lie. Greg pauses, then straightens himself up, massaging your legs. “Crud, I-I’m sorry, I—hold on, okay, I’m gonna get out for a second.” 

What? No, that’s not what you wanted, you wanted to stick with this. Before you can raise a hand, Greg reaches down and wipes away a tear from the corner of your eye. If that expression says anything, it’s that he’s not going to take no for an answer. Your left hand comes up and holds onto him as he shushes you, gently bringing his hips away. No matter how slow he goes, it’s still gripping you, like he’s going to turn you inside-out by accident. The head comes last, and it’s actually difficult, but Greg holds himself and tugs until the raunchy sound of the exit pops, and you feel your butt adjusting back to normal. It’s gonna take a couple minutes for sure. Even reaching down and rubbing gently won’t get rid of the pain. You’re reminded of the one time you tried to take a dildo in the shower, where the lube washing away made penetration difficult, and left you wincing in the lukewarm water.

“If it hurts you gotta tell me, babe, you gotta say something,” Greg murmurs, rubbing his hands up and down your sides. “You know I want this but I don’t want to hurt you. I mean, actually hurt you. I got a couple things to try out for myself, and trust me, I know what you’re going through.”

The thought of the man taking an ambitiously big dildo is enough to make you crack a smile, and you both laugh quietly before Greg sighs. You idly stroke yourself, watching his chest rise and fall. The line between his daddy modes is thinner than you thought. Two kinds of roughness, something like that. You clear your throat, and wipe your other eye. You ask if he wants to try again.

Greg frowns, and your stomach drops a little as you see that, for the first time, he’s uncomfortable. “I don’t know, I...I know it’s big, and I love how ambitious you are with all this but if you’re not gonna tell me when it’s too much then I’m…” he mumbles.

You didn’t come all this way to give up on daddy dick, and you definitely didn’t come here to make literally the nicest man you’ve ever met on an app feel bad. There’s plenty of things you can suggest, plenty that comes to mind. Your hands meet his as they’re going up your body, and Greg looks down at you with his eyebrows just barely raised.

**> > What will you say to him?**

**Notes for the Chapter:**

> Oh hm, what's this now? Until the next chapter is posted, YOU are able to send in submissions, IN-CHARACTER, to suggest what will happen next! Examples are up on the main Tumblr, short but sweet. How do you submit, then?
> 
> — Add a comment on this chapter! You can request it be anonymous as well.  
> — Go to www.a-night-with-mr-greg.tumblr.com, and send in a question/submission!  
> — Leave a response or DM on Twitter, @abel_after!
> 
> 2/13 EDIT: A response has been chosen, and chapter seventeen is up! Check it out.


	17. Speaking 'n Tongues

“Hey, he finally admits that it hurts a little,” Greg says, and he tries to smile, shaking his head. Maybe you’ve finally gone from being hotheaded to merely desperate in his eyes. But you’re neither, really, right? You’re not begging—well, not yet—and you’re certainly not angry. As much as you hate to admit it, you understand the decision to pause. Pain aside, what would you have done as a daddy, seeing someone in pain? The fact of the matter is that there’s only so much, and you still can’t stop from wincing a little as Greg straightens up.

The man clears his throat, as if clearing his head along with it. “Let your legs down a bit. C’mon, kid.”

Greg drags himself to the pillows, grunting as he pulls himself up onto the bed and lies down again. Moving takes away from the pain just a little, but this isn’t exactly the oral experience you were suggesting. Fingers in the mouth is one thing, eating his ass, well, as lovely as that would be it’s a little kinky for the calming down, and he knows it. And his penis would taste like a lube-and-you cocktail, not exactly pleasant.

All the same, as you work out where you’re being led, you see Greg open up his right arm, gently curling his fingers to bring you inward. For some reason there’s something a little sexy about the aspect of cuddling, even in the cooldown period. Sure, why not. You come up into the crook of the man’s hairy arm, letting him curl around you as you bring your right hand up over his torso. It’s warm, it’s slow, and he’s still stroking himself softly. The sound of sliding skin is slightly more moist, and his wrist glides a little, assisted by the oil. For you, it’s here and there, but with hookups a nice lubed-up finish happens more often than not. As long as you’ve both got it, might as well use it.

“Here’s your distraction.” The hand around you moves up somewhat suddenly to the back of your head. You inhale sharply as Greg brings your face to his chest, holding you close. This isn’t a dominant grip, but it’s firm, fatherly, like how you would imagine that a mother cat picks up a kitten by the scruff of its neck. In a similar vein, your lips brush up against the nub of flesh. Greg’s got meaty nipples, distinctly hairy like the rest of his chest, not massive but certainly distinct; they wouldn’t poke anyone’s eye out but they’d stand out under a muscle shirt, perhaps. The thought of the man in a tight shirt almost takes away from the fact that your arm is around the width of his gut right now.

As the hand slides away from your head, the order’s in place, and there’s nothing else you can do but open your mouth. One arm is stuck underneath your side as the other holds on tight, and you close your eyes as you start to gently mouth the man’s chest. The erogenous taste of skin is purely psychological, and you know that, and it tastes wonderful anyway. Your own nipples are inconsistent when it comes to pleasure, but they’ve never been hard-wired. Greg’s entire body rumbles like you’ve send an earthquake of nerves through him, and he grunts, sliding his hand down your body. In this position he can’t quite reach your ass, but he can hold you if you’re curled up.

“There, that’s a good boy,” Greg murmurs. “That’s a gentle boy. Daddy’s not gonna hurt you. Daddy’s gonna make you feel good. Let it all go, okay? Just take a second, just be my good boy for a bit. It’s okay. It’s okay…”

The pain is ebbing away naturally from your hole, still stinging but only marginally, and the words are helping in their own way. Being daddy’s boy feels good no matter what kind of daddy he needs to be. The arm stroking and squeezing you is strong, comforting, bringing you closer as you’re latched on. The skin filling your mouth as you suck and kiss is tinged with salt, stress leaving the body, a precursor to all the pleasure that will be going into your body later. Fuzziness from the body and belly extends into a metaphor, into your heart. You probably needed this just to get away from that stretch, but Greg needs it more, to ensure that you’re in a good place to try it again. With your eyes closed, you can feel his breath slowing down even as his heartbeat remains the same; after all, there’s still a lot of bloodflow happening elsewhere.

Elsewhere. Elsewhere, hm… Well, maybe a couple more minutes of this is nice, but there are other places to go, aren’t there? You know where you can go…

**> > Move to the other nipple across Greg’s chest**   
**> > Move your hand to his cock and take over the stroking**   
**> > Move up for a kiss and closer cuddle **


	18. Nip & Tug

**> > NIPPLE**

Double the pleasure, double the fun. As you gently pull your lips off of Greg’s nipple, pulling gently with your lips, you briefly wonder how he would treat two boys at once. Surely, once the two of you were ready, he could switch back and forth no problems. That’s the only issue with two bottoms, really, unless the other boy was more of a switch and Greg was more—well, it doesn’t matter for now. You’ve got a daddy under you, and that’s what matters.

The man makes no motion to stop you as you move your mouth over the breadth of his chest. Thin hairs, some graying and some still chestnut brown, graze your chin as you make your move. Of course Greg already knows where you’re going, and he hums under his breath as you nose the nub on the other side. Your left hand reaches up to steady yourself on his shoulder, and you have to pull yourself up to your knees, or almost up to there, with your right hand wrapped around the man’s body. He stops masturbating to hold you down to his chest with his left hand, as the right cups your buttocks.

“Mm, you like daddy’s tits?” Greg grunts. The hint of an edge is in his voice, the hard consonants of  _ tits, _ but not quite where it was when he was spanking you. “Makes daddy feel good, real good. Suck ‘em like a good boy?”

Already you’re moaning just a little under your breath. There’s just something about them, the point of the pectorals, the meaty, lovely button that’s so easy to pleasure and so easy to love. Your lips enfold the flesh and tug, and you know what? It’s time to get a little cheeky, or maybe it’s just what a good boy does. The hand steadying on Greg’s shoulder comes down to his other nipple, and you curl your left pointer underneath, pressing down with your thumb like you’re crimping the edge of a pie crust. Immediately you can feel the man shudder underneath you. As much as your submissive side has come out tonight, there’s nothing quite like the feeling of making someone so big tremble with pleasure at the push of a button. It’s easy to suck and rub in like kind, tugging with fingers and lips alike.

“F-fuck! God, yeah, that’s... _ooh,_ be gentle, baby, be gentle…”

This is about as gentle as you can get, but too much doesn’t feel that good; you just finished experiencing that first-hand. Keeping a steady pressure isn’t too hard, and it’s the consistency that makes it the most pleasurable, just like a normal massage, or a handjob, either one fits the bill. The massage at your back end is just as steady, gripping and pulling your cheeks apart. The finger is edging its way down towards the middle, but he’s keeping his distance still, not quite penetrating even though he wants to, probably. Each finger on the back of your head is doing its part as well, planting you firmly against the man’s nipple, forceful encouragement.

Gravity does its work well enough for you, and your right hand is free to roam once you raise it up and lean a little more onto Greg’s torso. The gut underneath you is strong enough to support a little leaning while your hand rubs around the base. Sweat and hair make trails, dark and matted, against the underside of the man’s belly where you can’t see. Sometime soon, you know you’re gonna have to get your face pushed under that again. For now, though, the turgid tip of Greg’s nipple is enough for your face for now.

The rest of you is getting some attention, but that’s not why you’re here. Determination fills you and your semi-hardon, and there’s gotta be a way to start the whole process over. You’ve left hookups before without sex, and it’s gone amicably before, nothing wrong with that. The real question is whether or not there will be things to keep you from a fate like last time. You gently bite down and close your eyes. Greg pulls at your muscles one more time with a deep sigh. When you look up, you can see his lower lip curling under his teeth for a second, the tongue rolling out over his skin. You tug on his right nipple one more time, and you can imagine, in that last little rugged gasp, there’s a mental connection, a tiny testament to what’s going to happen to you next.

**> > Let him start a finger or two, nice and loose to start.**   
**> > Hint at some face-sitting, and get his tongue up in there.**   
**> > Ask if he brought any toys that could relax your muscles.**


	19. Good Vibes

**> > TOYS**

Even though your mouth is slightly full, you know the muffled question reached him. It’s always interesting to see Greg blush, or at least look a little caught off-guard. “A-actually, yeah, I do,” he murmurs. “I got so caught up I didn’t even think about them. Well, one for now. Seemed like a little extra, eheh.”

Extra what, is the question. You raise your eyebrows, and Greg sighs softly through his nose. “You know, you see someone on here who’s got rope and straps and a whole rig they wanna set up. Didn’t know how much you expected.”  _ Just you, that’s all.  _ “Ha. Well, you’re sweet, I’ll give you that. But you already knew that, didn’t you.”

Now it’s your turn to blush. Greg gently rolls to the side to push your off to the bed, and you lie back obediently as he leans over. One quick kiss is all that passes for the moment, a silent I’ll be right back, a gentle little reminder. It’s not quite romantic but it’s loving in the way that any hookup can be loving. As he pushes himself off the bed, you check your lower lip and pull out a hair, wiping it on the side of the mattress. Body hair is wonderful as long as it stays on the body, that’s for sure.

You watch and rub yourself from the bed, your hands tucked between your legs, pressing your sore erection against your stomach as Greg walks back over to his overnight bag. A few seconds of rummaging and tugging later and he’s back with a small velvet-like bag. He stops and picks up the lube from where he dropped it, trying to hold everything as he opens up the bag as well. It’s an odd pouch for the vibrator, but it’s definitely fancy. You recognize it from your time wandering sex shops, all the times you’ve balked at the price tag. Seriously, who has that kind of money? Single queer dads, apparently. Greg smiles down at you, tossing the fancy bag back in the vague direction of his belongings.

“Scoot ya toot, kid.” You let the laugh bubble up, a natural giggle as you let him back onto the bed. He chuckles at his own little gag, lying back on the bed. With the dildo in one hand and the bottle in the other, Greg gets comfortable, letting out a larger sigh through his mouth. Turning his head, he nods. “Come on up, get on daddy’s belly. Gimme a bear cuddle.”

They’re simple orders, but you still have to pause before you can work out the image of exactly what he’s asking of you. Cautiously, though, you crawl around and get physically on top of him, laying down and hugging the man. He’s as warm as the first time you hugged, and you can easily slide your hips down until his erection warms your thighs. But that’s not why you’re here. Greg’s shushing you even though you’re not saying anything, little mouth movements to get you lower. Hair and skin rub against you as you lie down, as if you’re about to nap on top of him. Maybe once this is all over. Maybe.

“Tell me how it feels,” he whispers. You close your eyes. This is all going by touch now. The man holds your ass in one hand, pulling at the cheeks, tugging it and massaging it gently for his own pleasure as much as it is for your relaxation. The muscles still tense up involuntarily, but you’re both breathing in tandem, softly, to a point of calmness. If there is a power dynamic still, if your submissive horniness is occupying any part of your brain, it’s somewhere grumbling in the back, pissed that your body can’t handle the thickness.

A toy though, well, that’s a little easier. Even someone inexperienced could take something like that. It’s barely thicker than one of Greg’s fingers, but long and ergonomic, designed for pleasure. The man still goes slowly, though, running his hands up and down your back as your legs spread out to either side of his body. The lube starts off gently, a dollop on your backside, right onto the hole. Greg lets the bottle go and rubs with his free hand, like he’s massaging moisturizer into your skin. It’s water-based, if you had to hazard a guess, to be compatible with the toy. His fingers draw away, and you know he’s slicking up the toy with his hand movements, because neither one is touching you right now. When he finally starts it up, the sudden sound of the buzzing makes you jump a little, and Greg chuckles at the little twitch. “You’re okay, baby. Let daddy do the work.”

The penetration is gentle, and doesn’t happen all at once. Greg rubs and opens you with one hand, pulling the skin apart as he uses the other to insert the toy. The vibrating sensation is more or less exactly what you’d expect, except far more concentrated, far more powerful. If your cheap gel toy you had in college was a regular cup of coffee, this thing is a shot of espresso. Greg lets it slide in, breaking the rim easily, and you gasp despite yourself as the tip begins to slip past the ring. Your arms and legs tighten around the man as he kisses the side of your head.

He’s using the massager like an actual massager, pulsing it in and out, never exiting you but getting deeper with every motion back and forth. Greg lets his left hand hold your back, pressing you close to him, as his right fucks you with that fancy little toy. It slips back and forth against your walls, angled down towards the prostate, bent softly at the curve to hook inside your rectum and really get into the sensation. You’ve been fingered and teased before, but this is certainly different, and not at all unpleasant. It’s almost worth the money, and you know Greg’s getting his money’s worth right now. If you hadn’t been so rock-hard before, you might be dripping—or perhaps you are, still oozing gently onto the man’s belly underneath you. That’s the wonder of the love button, how well it responds to the pressure of a thick, black toy angled up against your body.

And thankfully, you’re feeling aroused again, more than aroused. It never stopped, but it’s not painful now, thank goodness. The rubs around your ring and the tender penetration are enough to make you forget why it even hurt in the first place. Yes, you know that Greg’s three times as thick, give or take, but that doesn’t matter. He’s grunting and humming underneath you, enjoying the teasing as much as you are. This is the daddy mood, holding you close and getting your hole ready. It’s a wonderful feeling, one that spurs your body to deeper desires…

**> > Slide down and get a nipple in, too.**   
**> > Pull up and make out with daddy.**   
**> > Sit up, push back, and ride a little.**


	20. Wordlessness

**> > MAKE OUT**

It’s a wavelength. It’s an idea. It’s that little spark that flies between you and links you together somehow. As soon as you bring yourself up, Greg’s mouth is already open, and his tongue meets yours with that same gentleness that you were thinking of without actually saying it. With the man warm underneath you, you lean into the kiss and hold him in the quiet of the room, two sets of lungs pausing under the sound of gentle rock.

The sexiness takes precedent, though, you could have guessed as much. The way that he’s still fucking you with that nice little dildo is enough to show. It’s more than enough, still a lovely buzz inside of you, still a wonderful exercise. The bottom that you thought you were is coming back out now, confident enough to start rocking your hips and doing it yourself. But, as one hand grabs your ass in warning, the other still holds you down to the dildo. Greg is in charge, no question. Not much you can do but revel in the kiss.

But that’s easy to do, isn’t it. He’s a sea of body heat, easy to hold onto as you pull your lips to and fro, and he does the same in like kind, almost amused. The tongues are only beginning to talk to each other again, a silent check-in to ensure that yes, yes you are very much ready for this, yes you want to taste him, yes you want to feel his facial hair pricking your own shadow. The tongue is a memory now as he uses it to pull you in closer, the tip tugging your lip, demanding as much as you can give him.

Returning sounds make you shudder on top of him. His low growls rumble up from his throat like a volcano. You know he does want to fuck you again, just like he did before, but he has to keep that animal on a leash. And it’s understandable, but you can’t help but moan in like kind, gasping for a little bit of air, and your twin groans come together once more. The reverberation is distinctly masculine in the best possible way, with no baggage, no observers, just two iterations of the sounds of men, deep bestial noises that make you tremble as you ride the dildo.

He’s getting a little deeper, a little more aggressive, but not to the point where you could actually call it ‘aggressive,’ not like before. The speed at which Greg’s loosening you is certainly greater than before, enough to make you whine into his growls, and he grunts louder now as your tongues play together. The girth of his muscle pulls you in, entwining as drool seeps out from between the locked lips and drips into his goatee. Greg uses the toy in time to the music, rolling penetration on-beat, before occasionally surprising you with a deeper dive. You can barely hear the buzz, but you can feel it and feel the change in frequency as it sinks into you.

Maybe you’re ready. God, are you? You want to feel ready. Daddy’s got your ass in both hands, using it and squeezing it ferociously in like kind. If Greg wants it, he isn’t saying it, but his body is making the motions that his mouth can’t, not with your tongue in it already. You wiggle back as you kiss, and he grunts in return, digging his fingers into you. It’s impossible not to want it right now. Your balls are begging you for some sort of release, and if you go back home and masturbate without cumming in this room, with this man inside of you, then you know your orgasm will be morbidly disappointing. It’s the moment, always, the moment that makes the climax worthwhile. Perhaps it’s selfish. Perhaps you can just masturbate together. But it’s worth trying again.

You pause the kiss and draw up, two open mouths close to each other. You say that you want it, barely verbal, words dripping from your lips like the sweat down your spine. Greg listens with closed eyes as you tell him how much you’re ready, how you want to try again. He doesn’t sigh, or grimace, or even smile as he opens his eyes to you. With a steady arm, Greg switches the toy off and gently tugs it out from where he’s lodged it up in your hole; a shudder runs through you.

“I know you want it, baby boy,” he whispers. The hand that held the toy vanishes to the side for a moment, and your stomach knots up as you hear the sound of it grabbing the lube bottle. There’s the wheeze of the air, a pause, and then Greg’s arm starts to move as wet, _schlk_ ing sounds fill the air. “I know you want it. Show me.”

**> > Try to ride it facing him and his belly**   
**> > Turn around, and go reverse cowgirl**   
**> > Get off to the side, try and coax him over**


	21. The Long Ride Home

**> > REVERSE**

Show, don’t tell. He’s all wet, you’re much more practiced than the last time, and most importantly, you’re on top. Having a two-hundred-plus man (if you’re guesstimating) on top of you is, to put it mildly, hot, but all things considered putting on a show for Greg is pretty excellent too. A smirk turns into a smile, a nervous one, as you back down just a little to feel that familiar thickness. Both of you pause.

It’s not the moment of truth, but it’s damn close. This isn’t the toy, and it’s not a random hookup like the others, and he’s not the smallest man. Greg nods at you, somewhere between **you can do it** and **there’s never any shame in bailing.** You take a deep breath. This is different now. You’re no longer clouded by the stream of terrible horniness that made you start too fast in the first place. You still feel the slickness, the tingling inside that rubbed right up against your prostate. Being a good boy is about knowing your limits, but about pushing them healthily, too. After all, if you want to take daddy, you’re going to have to take more than the average bear. Well, cub, boy, whatever. If you had the capacity to joke, you’d know that Greg would laugh at that, wouldn’t he.

But he’s no laughing matter. Showing off is just as good when you’re in control. You slide partially to the side, getting on your knees as Greg lets his hands slip away from you. He holds himself, stroking softly as you turn around and get on your knees. You lift one leg, bringing it over as Greg shifts farther away from the side of the bed. Spreading out so that you’re straddling his thighs isn’t easy with thighs like that. Spreading in general is hard with him. Still, with a leg on either side, you start to back up.

A finger meets your hold, playing with just the tender end, before Greg lets go of himself and grabs with both hands. He swears under his breath, thumbs digging into your flesh as you close your eyes. There’s no point in looking, not when you’re facing away and all you can see are his hairy legs; admittedly sexy, but not what you’re after. The hands shake your flesh, like he’s testing a firm set of melons at the grocery store. He brings you down, rubbing the underside of his glans over your hole, a preview of what’s to come. Just like before, it still feels too big.

Greg seems to sense that, actually, and one hand grabs the bottle again, popping it to squeeze a little more between your cheeks. The lube runs down, and Greg holds you steady with one hand as he moves his cock with the other. Sticky noises, oiled flesh on oiled flesh, echo underneath you as the head moves down. You force yourself to breathe. It’s a different angle, with gravity assisting you, with your legs in control.

The head pushes against your hole, spreading as the sphincter resists yet again. You let your body rock back as Greg leverages himself into you. “That’s right, that’s good, nice and slow, let daddy get in nice and slow,” he murmurs.

Slow will only get you so far, though. Biting your lips has been bad in the past, and you can’t hold onto anything but the bedsheets. Taking a deep breath, you force your body to relax as you push and force your muscles to give way, giving yourself just enough of a second to take in the girth of Greg’s cockhead before it slides into your ass. ‘Slide’ is accurate, slick and fluid and with as much grip as your hole will allow. All the same, the size and the pain is still absolutely there, the intensity of a fat, firm dick pushing into you. The edge of his head, with the skin pushed back, almost locks himself inside of you as you let out a soft moan, almost a whine, involuntary and satisfied. You can feel Greg pushing you apart, stretching out the soft walls, one inch at a time. There’s no vibration, but there’s the implication of throbbing, the blood rushing to your bodies’ most erogenous zones.

Both hands move towards your hips as Greg growls and holds you in place. Even with you on top, he’s still in control. The man adjusts himself under your legs, spreading until he’s in the best position he can be to get up in you. But now’s not the time for thrusting, both of you know that. It took a bit to get him inside, and yes, you know he wants to wreck your hole, but not if it’s gonna hurt you.

“F-fuck, you’re so tight, boy, my good boy, taking daddy like a champ,” Greg says, husky and shaking and as full of lust as you are. “Daddy’s gonna get all up in you. Ride daddy’s cock, good boy…”

You brace yourself against the sheets, getting your back in place as both your steady breaths fill out the room. His vocals are deeper, yours more measured, and you know you want it all in time. Every part of you is ready for him, even though you’re not quite all the way hard; the dripping from your own cock onto the bedspread is enough to show that yeah, you’ve been milked a little from the sheer thickness. Once he goes into motion, it’s possible your prostate will bear the brunt of it. But hey, he’s still giving you control over how you want this. The stench of sweat begins to rise from between his thighs. It’s time to get the ball rolling.

**> > Hilt yourself all the way, then see where things go from there.**   
**> > Start rocking at this depth, build up to the main event.**   
**> > Pull out, then go back in, get used to the size and tease him a little.**

**Notes for the Chapter:**

> If you'd like to vote, head over to @abel_after on Twitter or on Tumblr @a-night-with-mr-greg for updates!


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